Coach's Cutie Ch. 01

of that would be so fascinating, and it would almost certainly turn me on. Is that bad?"

Greg (in a joking tone): "Okay, well I'm guessing if the defendant and the victim's relationship is getting you all horny, that might affect how impartial you'll be able to be as a juror, right?"

Ah. He made a joke. That's a really good sign!

Me (poking Greg while laughing): "I could still be a fair juror! You don't think I could??"

Greg (smiling): "I'll tell you what, I would love to be waiting for you in bed after you got through a full day's worth of hearing testimony as a juror in this imaginary trial."

Me (feeling really good right now): "Well if I ever get a jury summons, you'll be the first to know."

Me (giving Greg a kiss): "Okay, so I just told you something mortifying about me... so I think it's your turn now. And I want something better than..."

Me (doing a bad impression of Greg's voice): "Uh, I enjoy pleasing women with oral sex."

Greg (laughs): "Ha ha. I know I'm predictable. But seriously, if I had something to tell you, I would definitely tell you. I just don't have anything that can remotely compare with your fantasy about being a juror in a real life episode of Law & Order SVU. I wish I did for your sake, but I don't."

Me: "Okay, okay. I know. I'm definitely not trying to make you feel bad or anything, that's for sure."

I give Greg another little snuggle and now I start caressing his bare chest with my right hand.

Me: "So it doesn't have to be a fantasy per se, but what about like a specific type of porn? Do you have any unusual or interesting fetishes or types of adult videos you like to watch?"

Greg (exhales): "Ohhhh... I don't know. I don't think so? If I do watch porn, it's mostly normal stuff. Although, I do have a preference for anything amateur or homemade compared to movies with porn stars. The whole giant fake boobs with terrible acting just doesn't do it for me. I prefer something that actually seems real?"

Okay, Greg's preference in porn for realism over fakeness is definitely understandable, but that still doesn't give me much to go off of. I think it's time for me to try a completely new angle here.

Me (in a softer tone): "So tell me about coaching. How did you end up as the girls coach and not the boys?"

Greg (chuckles): "I see where this is going now, ha."

Greg (smiling but with a little bit of nervousness): "It definitely isn't very scandalous. I actually used to coach the boys team, but then... do you remember meeting that guy named Craig, like a couple weeks ago when we were standing outside the gym? He's the coach of the boys team now?"

I'm not sure who that is or when that was, so I shake my head no.

Greg: "Well anyway... he came in like three years ago, and he was interested in coaching. And he was like this big shot college basketball player many years ago, so I think they basically gave him the boys team out from under me."

I didn't know any of this, but that kind of sucks!

Me (genuinely): "Aw, I'm sorry. I wish I remembered meeting this guy now, because I really don't like him!"

Greg (chuckling): "Oh it's not a big deal, and the old girls coach was actually retiring from teaching at that same time, so they phrased it as nicely as they could, saying it'd be a great opportunity for me to follow in her footsteps with the girls team as she was kind of a legend."

Me: "Oh, so they offered you the girls coaching position so they could offer this Craig guy the boys team?"

Greg: "Yeah, basically. But it's been great. In some ways I actually prefer coaching the girls, anyway. They're more focused on actually playing basketball, and less on filming slow-motion Tik Toks of themselves attempting ridiculous alley-oops they don't have a prayer of making, anyway. Ha."

Me (reaching my hand inside of Greg's underwear now): "Plus, it's probably more fun to hang out in the girls locker room than the boys, right?"

Greg (chucking): "Yeah that's not a thing. Maybe when we were growing up that might've happened, but in this day and age, there's no way I'm ever stepping foot inside their locker room."

Me (genuinely curious): "Seriously? So how do you meet with the team like at halftime or something?"

Greg: "There's a common area between the two locker rooms where we gather. And if the girls are in their locker room and we need to get them or something, I'll send Claire in."

Me (I know this is a ridiculous question): "But Claire's gay, right? How is that any different from you going in there?"

Greg (giving a small shrug): "I don't know, that's just how the world works?"

Me (starting to fondle Greg's soft penis inside of his boxer briefs): "That's not really fair, is it now?"

Greg (laughing): "You're right. I should probably go complain to the administration. Excuse me, you know how our assistant coach Claire, she's a lesbian? Well she likes vaginas, and I like vaginas, so why does she get to see these high school girls changing and I don't?!? That's so unfair!"

Me (laughing now too): "Yeah, you should definitely ask for a meeting about that. You bring up some good points! In fact, can I be there at the meeting?"

Greg (still chuckling): "You can't be at the meeting, but maybe you'll be on my jury when they charge me with a crime just for asking about this."

Me: "Oooh perfect, I would love to be on the jury that gets to decide your fate. I'll definitely make sure to get you off."

Me (whispering into Greg's ear): "I'm good at that."

Greg laughs, and I have to admit it was one of my better jokes I've made recently. But I can't help but notice that despite all my fondling, Greg isn't getting the least bit hard. Apparently he notices this as well.

Greg: "Sorry my dick isn't responding. I'm guessing it's the alcohol as I obviously don't drink very often."

Oh I'm well aware how you don't drink much. And it's honestly not a big deal, but harder would be better right now. If for no other reason than trying to stroke a limp penis just isn't very satisfying, for either the cock or the hand!

Me (sticking with the coaching aspect some more): "So who's the prettiest girl on your team?"

Greg (answering rather quickly): "I think most people would say Amanda."

Me (intrigued by his rapid response): "Interesting. So who's Amanda and what's she look like?"

Greg: "She's actually going to be our best player this year. She's tall. She's a forward. Great scorer. Above average rebounder. She's got long, light brown hair. She's very popular, not just on our team but in the whole school. Like I'm pretty sure this spring she'll end up being the prom queen. Plus she's dating this kid Lucas, who's the star of the football team and everything. So they're definitely like a power couple."

Me (still diligently stroking away): "So Amanda and Lucas. Nice. So do you think they're fucking?"

Greg (with a limp cock that's still not responding to my efforts): "Uhh, probably? Yeah I guess. I'd be surprised if they weren't, you know."

Geez, this is like pulling teeth! Painful. Now, a moment ago, Greg did say that 'most people' would think Amanda was the best looking girl on the team. But knowing Greg and how pedantic he can be, I can't help but wonder if there's a reason he used that specific phrasing.

Me (taking a stab here): "So you just said that most people would say Amanda was the prettiest girl on the team, but I'm actually not concerned with what most people might think. I'm curious what Coach Greg thinks. Who does Coach Greg think is the most attractive girl on his team?"

Greg: "Oh. Uh. I don't know."

I see Greg kind of look up at the ceiling in thought. And then I feel it. It's subtle. It's not a huge change, but I definitely finally feel something happening to the penis I've been so desperately trying to get a response out of.

Me (as Greg's penis, while still soft and malleable starts filling up in size ever so slightly): "Is there maybe a girl on your team, that doesn't get the attention that Amanda does, but maybe if you were still in high school you'd probably have a thing for?"

There it is. His cock is straightening up. There's absolutely no doubt about it now! I'm definitely onto something here.

Greg (sounding a little nervous): "Oh, I don't know. Maybe?"

We both know full well there's no maybe about it.

Me (while finally able to get a real stroke going): "What's her name?"

Greg (still pointlessly holding out hope I'm going to drop this line of questioning); "Whose name?"

Me: "The girl on your team, who doesn't get nearly as much attention as she should."

Greg: "Well there's this one girl..."

Yep, Go on...

Greg: "Her name is Madison."

Jackpot. Eureka. Use any exclamation you want. I found something! And oh by the way, Greg is absolutely, 100% completely hard right now.

Greg (exhaling as if my hand job is starting to make him feel pretty good, too): "...but everyone calls her Maddie."

I take my hand off of Greg's cock, but only so I can use both hands to slide his underwear down and off his legs. Now he's completely naked.

Me (returning my hand to Greg's shaft): "So tell me about Maddie. I want to know everything about her."

Greg (turning his head to look right at my face): "I don't know. This is kind of weird."

Me: "It's not weird to me. It's actually really fucking hot. So what's Maddie like?"

Greg: "Okay. Well... Maddie has curly blonde hair. She's really, really nice. And she's smart. And she's a hard worker. She doesn't play much, but I'm sure she'll get in most games this season when our starting guards need a break."

Me: "So she's also a guard? So that means she's smaller?"

Greg: "Yeah, she's not very tall. She's quite petite actually."

Me (starting to pump a little harder now): "So, she's a little, curly-haired, blonde cutie? Does that sum it up?"

Greg (looking right at me with his mouth hanging open slightly): "Yeah, that's her."

I've noticed, not just with Greg here, but with other guys I've dated since my divorce, that they seem to get really turned on by the idea of a petite girl. I think it must play on some sort of hunter/gatherer primal instinct of men, where being with a smaller female makes them feel all big and strong. I'm sure not all guys are like this though, as some may very well prefer the exact opposite body type, but a number of the men I've dated definitely seem to.

Come to think of it, a lot of it is probably just the guys that I'm actually dating. Considering I'm on the slender side of the spectrum myself, I'm probably just inherently attracting these types of guys? Oh well. Either way, it sure seems like Greg continues to fit this pattern.

Me (still jerking): "So does your little cutie have a boyfriend?"

Greg: "I don't know."

Me: "Why don't you know? You knew about that Amanda girl's boyfriend, Lucas, the football player, right?"

Greg: "Everyone knows about them. Even the teachers. Nobody gossips about Maddie's love life."

Me: "Fair enough. So do you think she's still a virgin?"

Greg: "I don't know. Maybe?"

Me: "Based on how she looks?"

Greg: "No. She's cute enough that I'm sure she gets attention from some of the boys. More based on how she acts."

Me (intrigued by this comment): "Oh, she's kind of a prude?"

Greg: "No. She's not a prude or super religious or anything that I know of. More that she seems to be kind of a goody-two-shoes, or a teacher's pet type? You know what I mean?"

Me: "Yeah I can picture it. And I can also see how you'd be intrigued by a cute little rule-follower, considering you're such a rule-follower yourself."

Greg (breathing heavily now): "Yeah, I kind of like that she's like that."

Me: "And so is she pretty obedient? Does she always do what you tell her to do during practice?"

Greg (getting an intense look in his eyes now): "Yeah, for sure. She's always the first to line up, or the first one to listen whenever I ask the team to do something. And she was the same way when I had her in class a couple of years ago."

Me (really getting excited about this now): "Oh, so you were her teacher before?"

Greg (panting): "Yeah... in 10th grade."

Me: "It's really hot to think about how much this girl must want to please you. You used to be her teacher, and now you're her coach. She's probably always looked up to you, and now you even get to decide whether she plays in the games or not. That's a lot of power you hold over her."

Greg: "I know. But she's so nice. I would never abuse that power or hold anything against her."

Me (seductively): "Of course you wouldn't. You would never want to do anything mean to her, now would you?"

Greg (desperately): "No. Never."

Me: "Of course not. Instead, you'd probably want to do something nice for her, now wouldn't you?"

Greg (panting): "I don't know. What do you mean?"

Me: "Would you want to make her feel good?"

Greg (still breathing heavily): "Yeah."

I don't say it out loud, but I'm so unbelievably curious to know what this Maddie girl is like. I'm curious to know what she looks like. I'm curious what kind of body she has. I'm curious what her voice sounds like and how she and Greg act around each other. All of this is so fucking fascinating!

Right now though, all I care about is making sure that Greg orgasms, and that he cums so hard while we're talking about his little crush, Madison.

Me (really slowing down my pumping but squeezing his shaft nice and tight): "Oh I'm pretty sure you could make Maddie feel sooooooo good if you wanted. You could lean her back, right here on this bed. Then you could slowly pull down her little, satin basketball shorts, before gently taking off her soft, innocent, cotton underwear. And then finally, once she was totally bottomless, you could take ahold of her cute, little knees and spread her thin, soft legs completely open."

Greg's lower jaw is dangling so low right now, and while he isn't saying anything, he's staring at me so intensely.

Me (continuing): "I mean, given how obsessed you are with eating me out, I can't even imagine what you'd do if you got a chance to devour Maddie's tiny, little, virgin, blonde pussy. Am I right?"

Greg (under his breath): "Oh my god."

Me: "So what do you think she would taste like? Can you even imagine what it'd be like for your tongue to make contact with her bright pink opening as you finally get to enjoy her tangy, sweet juices?"

Greg (extending his head back): "Oh I'm cumming. I'm fucking cumming."

Wow. That was fast!

I keep a tight hold on Greg's cock, while I focus on giving him the last few pumps needed to bring his orgasm through to completion. But after a few seconds pass, I've only seen one relatively minor squirt of semen come out, so I decide to adjust my grip to get a better angle.

Greg (with a huge exhale): "Uggghhh... Ohhhhhh..."

Holy shit. Three consecutive enormous globs of Greg's cum go shooting straight up into the air, and I realize now that I must've been holding him so tight a second ago, I was actually stifling his orgasm, not helping it! Ooops!

But based on Greg's look of total elation and relief right now, it seems like he's already forgiven me. One of the large squirts of jizz lands right back down onto my wrist, so I quickly smear that cum up and down his shaft to give me some extra lubrication for my last few jerks. Another couple of dribbles come out, and as I start to wind down the pumping of his now cum covered cock, I can tell from Greg's breathing that he's just about done, too. I let go of the glistening shaft and start to asses the glorious mess we've just made.

Greg's jizz is everywhere, so I reach over to my bedside table to the strategically placed box of tissues I keep there. I grab a bunch, and then start wiping up first my hands, then Greg's chest, and finally up and down his still mostly hard shaft.

Greg (quietly): "Oh my god. Oh shit. Oh shit."

Based on his post-orgasmic reaction, I'm guessing he enjoyed our little discussion just as much as I did.

Greg (a little louder now): "Oh shit. That wasn't right. That was a mistake."

Wait. What?!?

Me (sweetly): "Are you kidding? That was amaaaaaaazing. It was so hot."

Greg (clearly a little distraught): "I shouldn't have said those things. Becca, I shouldn't have told you any of that."

Okay he's panicking. It's going to be okay though. I can handle this.

Me (leaning in to give him a kiss): "Greg, there is nothing wrong with what just happened. I promise. It's totally normal to have thoughts like that, and I love the fact that you were able to share them with me."

Greg: "I know thoughts are just thoughts, but it's still wrong of me to think like that."

Me (determined to fix this): "Okay... hold up. First off, how old is this Maddie girl? What year is she?"

Greg: "She's a senior. She's 18."

Me: "Okay, perfect, she's a senior. But how do you know she's 18? Do you know for a fact she already had her birthday this fall or something?"

Greg: "Yeah, her birthday is September 16th."

Woah. He knows her exact birthday?!? Not the time to rag on him for that, so I'm going to let that slide for now, but that is fucking hilarious.

Me (sympathetically): "Oh, okay. Good. Just curious, how do you know her birthday?"

Greg (realizing now that what he just said is kind of weird, so he immediate gets a little defensive): "I only remember because when she was in my class in 10th grade, her friends made a big deal about it. And the reason they made a big deal was because she was the first of them to get their license, which means a little over two years ago she had turned 16. So she's definitely 18 now."

Wow. A lot to unpack there but I'm definitely not asking any follow up questions. I mean, it's one thing to remember that her friends made a big deal about her birthday, but it's taking it to a whole 'nother level to notice on that day what the actual date is, and then to still remember that exact date more than two years later! Somebody's got it real bad for little Madison it appears. And I love it.

Me (totally placating my boyfriend): "Okay yeah, that makes sense. And so if she's definitely 18, then this little conversation we just had a few minutes ago is not a big deal at all. In fact, it's absolutely, 100%, without a doubt, totally fine."

Greg (starting to calm down a little): "Okay. I guess. But you have to promise not to ever tell anyone... like ever... okay?"

Me: "Absolutely. I swear to god I won't. And I expect the same of you and my SVU jury fantasy, too. Eh?"

Greg (chuckling, thank god he's actually laughing now): "Yeah, no worries there. I wouldn't even know where to begin in trying to explain that one."

Me: "Then it's a deal."

Me (giving Greg a kiss): "You had said your first basketball game of the season is this upcoming Friday, right?"

Greg (clearly sensing what I'm getting at): "Oh god. I assume you're definitely coming to it now?"

Me (excitedly): "I was planning on going to it before I learned about any of this. But now... I wouldn't miss it for the world!"

Greg (half joking but I think half serious): "Just promise me you won't do or say anything weird... about... you know... like no subtle comments, or innuendos, or anything at all? Okay?"

Me: "I know what you're getting at, and I definitely won't."

Me (smiling now): "Well... I probably won't."

I give Greg another kiss, but he doesn't really kiss me back as instead he has kind of a deer in headlights look to him.

Me (sweetly): "Relax, Hon. That was a joke. I swear to god your secret crush on Maddie is safe with me."

Greg (now gives me a kiss): "Okay. Thanks. Even just hearing you say her name out loud is making me anxious."

Yep, I definitely need to desensitize him. Still a lot of work to be done!

Me (playfully): "Maddie, Maddie, Maddie. I can't wait to see this cute little Madison, and how hard she plays for her big, strong coach."